Tetrahydrofuran → HCID 178524819, compound

HRID 408787Notes

Reaction equation

HRID 408787 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([Cl:33])[C:21]([S:23](=[O:32])(=[O:31])[NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:22][C:16]=3[N:15]=2)[CH:13]=1)=[O:8])C.C1COCC1>O>[Cl:33][C:20]1[C:21]([S:23](=[O:32])(=[O:31])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:22][C:16]2[N:15]=[C:14]([N:12]3[CH:13]=[C:9]([C:7]([OH:8])=[O:6])[CH:10]=[N:11]3)[NH:18][C:17]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178469991HCID 178469991, compound

Product 1

HCID 178524819HCID 178524819, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Lithium hydroxide monohydrate (7.90 mg, 0.188 mmol), 1-(6-chloro-5-phenylsulfamoyl-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (28.0 mg, 62.8 μmol), THF (0.24 mL), and water (79 μL) were combined, briefly sonicated, and left to stir at 23° C. for 18 h. Solvent was evaporated and 2 mL water was added. This solution was brought to pH 1 with aqueous 1M HCl and the resulting precipitate was collected and dried to yield the titled compound (20.6 mg, 75% yield). MS (ESI/CI): mass calcd. for C17H12ClN5O4S, 417.0; m/z found, 418.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6, tautomeric broadening): 13.96 (s, 1H), 13.02 (s, 1H), 10.55 (s, 1H), 8.91 (s, 1H), 8.33 (s, 1H), 8.31-8.08 (m, 1H), 7.95-7.53 (m, 1H), 7.26-7.04 (m, 4H), 6.96 (t, J=7.2 Hz, 1H).

Workup

  1. custombriefly sonicated
  2. waitleft
  3. customSolvent was evaporated
  4. addition2 mL water was added
  5. customthe resulting precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-58b334a0a2df465daf9e43d83d0949e6
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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